4 Rolling Rd, Chestertown, MD 21620
OFF MARKET

$290,700

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,950 sqft

4 Rolling Rd, Chestertown, MD 21620

Est. Refi. Payment $1,741/mo*
Refinance Your Home
Currently Off Market - Sold Jun 4, 2020 for $145,000

Home Value

Trulia Estimate
$291K
Since last month
Decreased$3K (-0.9%)
Since last year
$100 (0%)
Since last sale
Increased$145K (+99.9%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +117% in the last 10 years
MonthEstimated value
2026
August 2026$290K
July 2026$292K
June 2026$297K
May 2026$296K
April 2026$292K
March 2026$289K
February 2026$285K
January 2026$292K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
204 Rolling Rd, Chestertown, MD
0.20
Single-Family Home
$340,000
03/19/26
3
2
2,296
201 Birch Run Rd, Chestertown, MD
0.12
Single-Family Home
$430,000
05/29/26
3
2
1,588
206 Barroll Dr, Chestertown, MD
0.22
Single-Family Home
$438,000
09/30/25
3
2
1,820
205 Pine St, Chestertown, MD
0.36
Single-Family Home
$296,337
09/30/25
3
1.5
2,212
224 Valley Rd, Chestertown, MD
0.21
Single-Family Home
$455,000
10/21/25
3
2
1,886
101 Birch Run Rd, Chestertown, MD
0.18
Single-Family Home
$475,000
12/11/25
3
2
1,961
303 E Campus Ave, Chestertown, MD
0.24
Single-Family Home
$364,000
01/16/26
3
2
1,532
521 N Kent St, Chestertown, MD
0.28
Single-Family Home
$365,000
07/22/26
3
2
1,934
217 Philosophers Ter, Chestertown, MD
0.39
Single-Family Home
$370,000
05/01/26
3
1.5
1,404
411 Greenwood Ave, Chestertown, MD
0.27
Single-Family Home
$415,000
01/07/26
3
2.5
1,676

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
5 Rolling Rd, Chestertown, MD 21620
0.01
$279,800
3
1
1,202
Off Market
1 Reed Ct, Chestertown, MD 21620
0.07
$420,400
4
2.5
1,854
Off Market
114 School Rd, Chestertown, MD 21620
0.13
$293,400
3
1.5
1,102
Off Market
201 Birch Run Rd, Chestertown, MD 21620
0.12
$430,000
3
2
1,588
Recently Sold
209 Birch Run Rd, Chestertown, MD 21620
0.14
$599,100
4
3
2,488
Off Market
109 Birch Run Rd, Chestertown, MD 21620
0.14
$483,500
3
2.5
1,428
Off Market
207 Glen St, Chestertown, MD 21620
0.16
$412,400
4
2
2,236
Off Market
110 Birch Run Rd, Chestertown, MD 21620
0.17
$613,900
4
3
2,672
Off Market
403 E Campus Ave, Chestertown, MD 21620
0.17
$304,200
3
1
1,248
Off Market
101 Birch Run Rd, Chestertown, MD 21620
0.18
$475,000
3
2
1,961
Recently Sold
204 Rolling Rd, Chestertown, MD 21620
0.20
$340,000
3
2
2,296
Recently Sold
101 School Rd, Chestertown, MD 21620
0.21
$364,200
3
1.5
1,424
Off Market

Local Information

  • Map ViewExplore the area around 4 Rolling Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1961
Living Area
1,950 sqft
Price/Sqft
$149

About this House

This single-family home is located at 4 Rolling Rd, Chestertown, MD. 4 Rolling Rd is in Chestertown, MD and in ZIP code 21620. This property has 3 bedrooms, 2 bathrooms and approximately 1,950 sqft of floor space. This property has a lot size of 9099 sqft and was built in 1961.
4 Rolling Rd, Chestertown, MD 21620 is a 3 bedroom, 2 bathroom, 1,950 sqft single-family home built in 1961. It last sold for $145,000 on Jun 4, 2020. More recently, it was listed as a rental in January 2015 with an asking price of $1,200 per month. That rental listing was removed on January 31, 2015. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $290,700, with a rent estimate of $1,891/month.

Home Details for 4 Rolling Rd

Interior Features

Interior Details
BasementTypes of Rooms: Family Room, Pantry, WorkshopCeiling Fan
Heating & Cooling
Heating: Heat Pump, ElectricAir ConditioningCooling System: CentralHeating Fuel: Heat Pump
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood
Appliances & Utilities
DishwasherDryerMicrowaveRefrigerator
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: OtherExterior: Brick

Property Information

Year Built
Year Built: 1961
Property Type / Style
Property Type: Single Family HomeArchitecture: Conventional

Building

Levels, Entrance, & Accessibility
Disabled Access

Community

Units in Building: 1

Lot Information

Lot Area: 9099 sqft

Price and Tax history

DateEventPrice
Jun 4, 2020
Source: N/A
Sold
$145,000
Mar 4, 2020
Source: Agent Provided
Pending
$147,700
Feb 24, 2020
Source: Agent Provided
PendingToActive
$147,700
Jan 30, 2020
Source: Agent Provided
Pending
$147,700
Jan 10, 2020
Source: Agent Provided
Listed For Sale
$147,700

Market trends in Chestertown

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
59
5MoM

Around this home

What Locals Say about Chestertown

At least 34 Trulia users voted on each feature.

  • 85 % Say car is needed

  • 84 % Say there's holiday spirit

  • 83 % Say it's dog friendly

  • 77 % Say people would walk alone at night

  • 77 % Say parking is easy

  • 76 % Say yards are well-kept

  • 74 % Say it's quiet

  • 61 % Say neighbors are friendly

  • 57 % Say there's wildlife

  • 56 % Say it's walkable to restaurants

  • 54 % Say there are sidewalks

  • 49 % Say kids play outside

  • 46 % Say it's walkable to grocery stores

  • 44 % Say streets are well-lit

  • 41 % Say there are community events

  • 38 % Say they plan to stay for at least 5 years

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "Washington park is a great, safe and family oriented are!! I’ve never live there permanently but by mom is from that are and my grandparents still live there!! I live always visiting! And hope to have a hoke there myself one day!!!"
    1
    Flag
  • Trulia User
    "Short and very accessible. Everything is within 10 minutes and waterfront on the Chester river is spectacular"
    1
    Flag
  • Trulia User
    "I lived in this neighborhood for tens you’d and the community is very friendly. Community clean up after their dog and they watch over one another "
    0
    Flag
  • Kesha C.
    "Chestertown is okay area to live in. Its what you make it honestly. Nothing major or minimal happening."
    0
    Flag
  • Tracy W.
    "The schools are better in Queen Anne's County. The town is well-maintained, and houses and businesses in town have to meet the strict guidelines of the historical society. Restaurants are generally mediocre in quality and high in price. "
    0
    Flag
  • Rancraw
    "This is just a great place to live. I am from Dallas, TX, I have lived in six countries, DC, and Miami. This is my favorite place to live. ONLY down side is getting to an airport under an hour."
    9
    Flag
  • Acaldwell1297
    "I am basically on the main road.... pretty easy to get in and out. I don’t live far from work! So pretty easy for me "
    1
    Flag
  • Guillermo A.
    "Good Community, friendly people, good services. "
    0
    Flag
  • Nancy M.
    "People do not come to Chestertown because it is quite like everywhere else . . but because it is exceptionally itself."
    5
    Flag
  • asso
    "Quiet - not for night owls. Nice farmer's market, good library. Easy acess for weekends in DC, Baltimore, Philly, & Ocean Beaches. College town, Chester River"
    0
    Flag
  • Dafoster
    "Historic town along the Chester River and home to Washington College. Convenient to shops, restaurants, farmers market, waterfront, Garfield Center for the Arts and College Activities. A walker's paradise and a favorite for bikers and boaters."
    5
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 4 Rolling Rd

  • What is 4 Rolling Rd estimated to be worth?
    Trulia's estimated value for 4 Rolling Rd in Chestertown, MD is $290,700.
  • What is the price history for 4 Rolling Rd?
    4 Rolling Rd in Chestertown, MD last sold for $145,000 in June 2020.
  • Is Chestertown a buyer's or seller's market?
    Chestertown is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Chestertown?
    Residents describe Chestertown, MD as dog-friendly, easy to park in, and well-kept. Most residents say you need a car. See recently sold homes in Chestertown, MD.
  • Does 4 Rolling Rd have air conditioning?
    Yes, 4 Rolling Rd in Chestertown, MD has air conditioning.
  • Does 4 Rolling Rd have laundry facilities?
    Yes, 4 Rolling Rd in Chestertown, MD has laundry facilities.

Explore by feature - Pet Friendly

Explore by feature - Air Conditioning

Apartments for Rent

Skip to last item
Skip to first item

Off Market Homes Near 4 Rolling Rd

Skip to last item
Skip to first item

Homes for sale near 4 Rolling Rd

Skip to last item
Skip to first item
Skip to last item
  • Results are loading
Skip to first item